The first entry to pyrrolo[2,3- c ]quinoline-2,4(3a H ,5 H )-diones

Citation data:

Tetrahedron, ISSN: 0040-4020, Vol: 64, Issue: 19, Page: 4387-4402

Publication Year:
2008
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Repository URL:
http://hdl.handle.net/10563/1000871, http://publikace.k.utb.cz/handle/10563/1000871, http://hdl.handle.net/10563/1000952, http://publikace.k.utb.cz/handle/10563/1000952
DOI:
10.1016/j.carbpol.2007.07.001, 10.1016/j.tet.2008.02.063
Author(s):
Kafka, Stanislav, Klásek, Antonín, Polis, Jiří, Rosenbreierová, Veronika, Palík, Ctirad, Mrkvička, Vladimír, Košmrlj, Janez
Publisher(s):
Elsevier BV, Pergamon Elsevier Science Ltd.
Tags:
Materials Science, Chemistry, Biochemistry, Genetics and Molecular Biology, Pharmacology, Toxicology and Pharmaceutics, pyrrolo[2,3-c]chinolony, chinolinony, Wittigova olefinace, mechanismus, NMR, Pyrrolo[2,3-c]quinolones, Quinolinones, Wittig olefination, Mechanism, vyfukování, mechanické vlastnosti, plasikátor, škrob, termoplastický škrob, film blowing, mechanical properties, plasticizer, starch, thermoplastic starch
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article description
Wittig olefination of 3-aminoquinoline-2,4(1 H,3 H )-diones 1 with ethyl (triphenylphosphoranylidene)acetate (Ph 3 P CHCO 2 Et) afforded ( E )-3-amino-4-ethoxycarbonylmethylene-1,2,3,4-tetrahydro-2-quinolones ( E )- 2 and pyrrolo[2,3- c ]quinoline-2,4(3a H,5 H )-diones 3. An alternative approach for the synthesis of 3 via 3-bromoacetamidoquinoline-2,4(1 H,3 H )-diones 7, their corresponding triphenylphosphonium salts 8, and ylides A that undergo intramolecular Wittig reaction, was investigated. Under the applied reaction conditions, the phosphonium salts 8 and ylides A are so unstable that they partly decompose to 3-acetamidoquinoline-2,4(1 H,3 H )-diones 9 during the synthesis of 3.

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